ブチロニトリル

Nitrogen Compounds -> Nitriles

Flammable agents - 3rd degree

log Kow = 0.53

0.5/0.6

0.53

0.7936 at 68 °F (USCG, 1999) - Less dense than water; will float

0.8091 @ 0 °C/4 °C

Density of saturated air: 1.07 @ 38.4 °C (air= 1)

Relative density (water = 1): 0.8

0.796 @ 15°C

0.81

3 % at 77 °F (NIOSH, 2024)

Miscible with alc, ether, dimethylformamide

Sol in benzene

In water, 33,000 mg/l at 25 °C.

Solubility in water, g/100ml at 25 °C: 3

(77 °F): 3%

62 °F (USCG, 1999)

17 °C

76 (24 °C) °F (OPEN CUP)

17 °C

62 °F

244 °F at 760 mmHg (USCG, 1999)

117.5 °C @ 760 mm Hg

116-118 °C

117 °C @760 [mm Hg]

244 °F

-171 °F (USCG, 1999)

-112 °C

-112 °C

-112.6 °C

-170 °F

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P321, P330, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Danger

H225 (100%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P261, P262, P264, P270, P271, P280, P301+P316, P302+P352, P303+P361+P353, P304+P340, P316, P321, P330, P361+P364, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Chemical: Butanenitrile

Butanenitrile is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Butanenitrile are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 25-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/5838

Butyronitrile: HSNO Approval: HSR002924 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Special Hazards of Combustion Products: Toxic cyanide fumes (USCG, 1999)

· HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames.

Highly flammable. Gives off irritating or toxic fumes (or gases) in a fire. Above 17 °C explosive vapour/air mixtures may be formed.

FLAMMABLE, DANGEROUS FIRE RISK.

Dangerous fire hazard when exposed to heat, flame, or oxidizers.

Dizziness, rapid respirations, headache, drowsiness, drop in blood pressure and pulse, delayed symptoms. May cause cyanosis (blue-grey coloring of skin and lips due to lack of oxygen) (USCG, 1999)

· TOXIC; may be fatal if inhaled, ingested or absorbed through skin.

2411 131

2411 131

BUTYRONITRILE can react vigorously with oxidizing reagents, when heated to decomposition, it emits highly toxic fumes of cyanides and oxides of nitrogen [Sax, 9th ed., 1996, p. 609]. Nitriles may polymerize in the presence of metals and some metal compounds. They are incompatible with acids; mixing nitriles with strong oxidizing acids can lead to extremely violent reactions. Nitriles are generally incompatible with other oxidizing agents such as peroxides and epoxides. The combination of bases and nitriles can produce hydrogen cyanide. Nitriles are hydrolyzed in both aqueous acid and base to give carboxylic acids (or salts of carboxylic acids). These reactions generate heat. Peroxides convert nitriles to amides. Nitriles can react vigorously with reducing agents. Acetonitrile and propionitrile are soluble in water, but nitriles higher than propionitrile have low aqueous solubility. They are also insoluble in aqueous acids.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Use water spray, foam, alcohol-resistant foam, dry powder, carbon dioxide. In case of fire: keep drums, etc., cool by spraying with water.

Fresh air, rest. Half-upright position. Artificial respiration may be needed. Refer for medical attention.

Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Induce vomiting (ONLY IN CONSCIOUS PERSONS!). Give a slurry of activated charcoal in water to drink. Refer for medical attention .

· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.

· ELIMINATE all ignition sources (no smoking, flares, sparks or flames) from immediate area.

Excerpt from NIOSH Pocket Guide for n-Butyronitrile:

General First Aid:

(General first aid procedures)

ALCOHOL FOAM.

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped or safely confined. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Apply water from as far a distance as possible. Use "alcohol" foam, dry chemical or carbon dioxide.

Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste numbers D003 and P030 must conform with USEPA regulations in storage, transportation, treatment and disposal of waste. /Cyanide cmpd and Cyanides, not otherwise specified/

A poor candidate for incineration. /Cyanides/

Remove all ignition sources. Personal protection: self-contained breathing apparatus. Do NOT let this chemical enter the environment. Collect leaking and spilled liquid in sealable containers as far as possible. Absorb remaining liquid in sand or inert absorbent. Then store and dispose of according to local regulations.

The worker should immediately wash the skin when it becomes contaminated.

Work clothing that becomes wet should be immediately removed due to its flammability hazard.

N-butyronitrile is considered highly toxic and requires the same handling as other toxic nitriles.

All nitriles should be handled under carefully controlled conditions and only by personnel having a thorough understanding and knowledge of safe handling techniques. Because of the nature of nitrile cmpd and the lack of complete toxicity data on many nitriles, care should be exercised in handling these cmpd to avoid inhalation of the vapors, ingestion, and contact with the skin. /Nitriles/

For more Preventive Measures (Complete) data for BUTANENITRILE (7 total), please visit the HSDB record page.

Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Immediate precautionary measure

Antidotes to cyanide poisoning include hydroxocobalamin and sodium nitrite, which release the cyanide from the cytochrome system, and rhodanase, which is an enzyme occurring naturally in mammals that combines serum cyanide with thiosulfate, producing comparatively harmless thiocyanate. Oxygen therapy can also be administered. (L97)

P-AMINOPROPIOPHENONE PROTECTED MICE AGAINST LETHAL DOSES OF POTASSIUM CYANIDE, & MANY ORGANOTHIOCYANATES & ORGANONITRILES.

The toxic mechanism of nitriles and the effect of metabolic modifiers in mice were studied in relation to their physicochemical properties. All the test nitriles liberated cyanide both in vivo and in vitro, with the exception of benzonitrile, although the extent of liberation and the effect of carbon tetrachloride pretreatment on the mortality of animals differed among nitriles. From these results, test compounds were tentatively divided into 3 groups. In group 1, acute toxicity was greatly reduced by carbon tetrachloride pretreatment, in group 2, toxicity was not significantly changed or was somewhat enhanced, and in group 3, benzonitrile only, toxicity was clearly enhanced. The amount of cyanide was higher at death in the brains of mice given group 1 compounds, the level being comparable to that found in mice killed by dosing with potassium cyanide. The relation between log (1/LD50) and log p for the compounds in group 1 fitted a parabolic plot, while that for compounds in group 2 was linear. For most nitriles, the in vitro metabolism was inhibited when the incubation mixture contained either SKF-525A, carbon monoxide, or microsomes from mice treated with carbon tetrachloride. When mice were closed with ethyl alcohol, metabolic enhancement of nitriles was seen compared with the control. However, ethyl alcohol, when added to the incubation mixture, inhibited the in vitro metabolism of nitriles. /Nitriles/

Exposure to high levels of cyanide for a short time harms the brain and heart and can even cause coma, seizures, apnea, cardiac arrest and death. Chronic inhalation of cyanide causes breathing difficulties, chest pain, vomiting, blood changes, headaches, and enlargement of the thyroid gland. Skin contact with cyanide salts can irritate and produce sores. (L96, L97)

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from a log Kow of 0.53(2) and a regression-derived equation(3), indicates that butanenitrile is expected to have very high mobility in soil(SRC). Volatilization of butanenitrile from moist soil surfaces is expected to be an important fate process(SRC) given a Henry's Law constant of 5.23X10-5 atm-cu m/mole(4). The potential for volatilization of butanenitrile from dry soil surfaces may exist(SRC) based upon a vapor pressure of 19.5 mm Hg(5). Microorganisms hydrolyze nitriles predominately to carboxylic acids plus ammonium ions(6,7). A mixed microbial culture, isolated from an environment contaminated with organic cyanides and PCBs, utilized butanenitrile as the sole source of carbon and nitrogen(8). The mixed microbial culture was grown for 48 hrs at pH 7 with 1 g/l of butanenitrile; the final pH and ammonia concn were determined to be 8.69 and 74.6 umol/ml, respectively(8). Thus, butanenitrile may be expected to biodegrade in soil(SRC).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 46(SRC), determined from a log Kow of 0.53(2) and a regression-derived equation(3), indicates that butanenitrile is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon a Henry's Law constant of 5.23X10-5 atm-cu m/mole(4). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 10 hours and 8 days, respectively(SRC). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(6), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Microorganisms hydrolyze nitriles predominately to carboxylic acids plus ammonium ions(7,8). A mixed microbial culture, isolated from an environment contaminated with organic cyanides and PCBs, utilized butanenitrile as the sole source of carbon and nitrogen(9). The mixed microbial culture was grown for 48 hrs at pH 7 with 1 g/l of butanenitrile; the final pH and ammonia concn were determined to be 8.69 and 74.6 umol/ml, respectively(9). Thus, butanenitrile may be expected to biodegrade in water(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), butanenitrile, which has a vapor pressure of 19.5 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere(SRC). Vapor-phase butanenitrile is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 32 days(SRC), calculated from its rate constant of 4.98X10-13 cu cm/molecule-sec at 25 °C(SRC) determined using a structure estimation method(3).

The substance can be absorbed into the body by ingestion, by inhalation and through the skin.

inhalation, skin absorption, ingestion, skin and/or eye contact

Oral (L96) ; inhalation (L96) ; dermal (L96)

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

Dizziness. Laboured breathing. Nausea. Vomiting. Weakness. Confusion. Convulsions. Unconsciousness.

MAY BE ABSORBED! Redness. Further see Inhalation.

Redness. Pain. Blurred vision.

See Inhalation.

irritation eyes, skin, respiratory system; headache, dizziness, lassitude (weakness, exhaustion), confusion, convulsions; dyspnea (breathing difficulty); abdominal pain, nausea, vomiting

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

A product water effluent from a coal gasification facility in Hanna, WY was found to contain a butanenitrile concn of 267 ppb(1); retort water from a shale-oil processing facility in Rock Springs, WY contained a butanenitrile concn of 13 ppb(1). The concn of propionitrile in condensate retort water from an oil-shale processing facility in Colorado was 2.5 mg/l(2).

The Koc of butanenitrile is estimated as 46(SRC), using a measured log Kow of 0.53(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that butanenitrile is expected to have very high mobility in soil(SRC).

This action promulgates standards of performance for equipment leaks of Volatile Organic Compounds (VOC) in the Synthetic Organic Chemical Manufacturing Industry (SOCMI). The intended effect of these standards is to require all newly constructed, modified, and reconstructed SOCMI process units to use the best demonstrated system of continuous emission reduction for equipment leaks of VOC, considering costs, non air quality health and environmental impact and energy requirements. Butyronitrile is produced, as an intermediate or a final product, by process units covered under this subpart.

Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

150 MG/KG ADMIN IP TO RATS. HIGHEST ACCUMULATIONS OF BUTYRONITRILE & CYANIDES OCCURRED IN LIVER, STOMACH, INTESTINES, KIDNEYS, & TESTIS. BUTYRONITRILE WAS ELIMINATED IN URINE IN VERY SMALL QUANTITIES, & THIS ELIMINATION WAS SLOW.

All organs were found to contain n-butyronitrile, free hydrogen cyanide and combined cyanide. The highest average concentration of n-butyronitrile was found in the lungs, the highest free HCN concentrations were in the heart and brain. Similar findings, in an expected dose-response manner, were found after lower doses of the compound.

Used as an intermediate in the chemical and pharmaceutical industries; [HSDB]

Basic material in indust, chemical and pharmaceutical intermediates and products; poultry medicines

CHEM INT FOR BUTYRIC ACID, BUTYRAMIDE AND PHARMACEUTICALS, OTHER ORGANICS (EG, KETONES, ESTERS)

2023: 1,000,000 - <5,000,000 lb

(1977) PROBABLY GREATER THAN 4.54X10+6 G

(1979) PROBABLY GREATER THAN 4.54X10+6 G

All Other Basic Organic Chemical Manufacturing

Butanenitrile: ACTIVE